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Abstract
A-seco-triterpenoids with a methylketone group were synthesized from epimeric 3-hydroxy-3-methyl-1-cyano2,3-seco-triterpenoids of the lupane and 19,28-epoxy-18H-oleanane types, which were formed by a Grignard reaction. The resulting methylketones underwent under base-catalysis conditions an intramolecular cyclization to form A-pentacyclic -substituted alkenenitriles. The synthesized compounds included 3-methyl1-cyano-19,28-epoxy-2,3-seco-2-nor-18H-olean-3-one and methyl 3-methyl-1-cyano-2-norlup1(3),20(29)-dien-28-oate, which inhibited in vitro reproduction of human immunodeficiency virus type 1.
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